TW201200017A - Use of maleimide salts to control phytopathogenic fungi - Google Patents

Abstract

The present invention relates to the use of new and known maleimide salts for controlling phytopathogenic fungi, and also to methods for controlling phytopathogenic fungi in crop protection, in the household and hygiene sectors and in materials protection, and also to crop protection compositions comprising these maleimide salts.

Description

201200017 VI. Description of the Invention: [Technical Field] The present invention relates to the use of novel and known maleic imine salts for controlling phytopathogenic fungi, as well as for crop protection, household and health care, and materials. A method of protecting a plant pathogenic fungus, and a crop protection composition comprising the same of maleic imide salts. [Prior Art] Maleidinium salts are known per se (see c/version 1967, ie, 1559-1570); maleic imine dithiol (only 1 〇 nickel) The substance is also known (cf. c-heart w 2〇〇5, from 3380-3382). However, it has not been known that the maleic imide salts are biologically active and suitable for controlling plant pathogenic fungi in crop protection. In modern environmentally and economically (for example, active range, maternality, selectivity, rate of application, residue formation, and ease of preparation), the demand for modern fungicides continues to increase, and in view of possible resistance, for example, Question = Kyrgyzstan = This is at least in some respects, and the development of novelty agents that satisfy the demand is a persistent goal. [Summary of the Invention] The maleic imide salt of the following formula (I) was found. Class 201200017

(2/n X)m 〇——N I R 0 (i) where (a) Y1 is a group of the following formula (II)

(II), Y2 is a group of the following formula (III) RY.R8 7 , s person m, r7 (III) » m is l, n is an ionic charge of X, and X is an anion selected from the group consisting of cr or ruthenium , or (b) Y1 is a group having the following formula (II)

(II), Y2 is -S_, or m is 0, (C) Y1 is -s-, Y2 is -s-, M is 1, n is the ionic charge of X, and

X is selected from the group consisting of H+, Ag+, Co2+, Cu2+, Fe2+, Mn2+, s 4 201200017

a cation of Ni2+, Pd2+, Zn2+, and R1 is hydrogen; or a Ci_Cs_alkyl group substituted by the same or different substituents such as _, _Rio and/or -COR11 as needed; or c3-c7_ a cycloalkyl-based scvcv cycloalkyl group _CrC2, each of which may be substituted by a substituent of the same or different elements, a CKV alkyl group or a group, or a plurality of times; or an aryl group, an aryl group, or an A) group or Green lysine group, each of which is optionally substituted one or more times by a substituent such as the same or different halogen, cvc4-alkyl, Crc4-dentate, -COR11 or sulfonamide in the aryl moiety, "," , ",", ^, ^, "and independently of each other are hydrogen, ^^-alkyl, or phenyl or benzyl, each of which is optionally the same or different halogen, CrC4·alkyl, crC4_ Substituting an oxy or CrC4-pyrustyl hydrazine substituent one or more times,

Rl° is hydrogen, C--C4_alkyl, Crc4-alkylcarbonyl, or an aryl group which may be substituted one or more times by a substituent such as halogen, CrC4-alkyl or CrCp haloalkyl, and R is a hydroxyl group, C1_C4 - Alkyl or crC4-alkoxy, which can be used to control phytopathogenic fungi to give very good results. The maleidinium salts of the formula (I) according to the invention are particularly suitable for the control of harmful phytopathogenic fungi. The aforementioned compounds of the present invention exhibit particular antifungal activity and are useful in crop protection, household and healthcare applications, and material protection. The maleidanilide salts usable in accordance with the present invention have the general definition of 201200017 provided by formula (1); however, it is possible to preferentially use the maleidinium salts of the formula (I) wherein the groups have the following definitions. R1 is preferably argon; or a CrC6_alkyl group which is substituted one or more times by the same or different substituents such as sulphur, gas, desert, -OR10 and/or -COR11; or CrCV cycloalkyl or c3-C7 - a ring-based group - a CVCr. group, each of which may be substituted one or more times by a substituent such as the same or a different gas, a mercapto group or a trifluoromethyl group, or a phenyl group or a phenyl group (Crc4_alkyl group). Or a phenylsulfonylamino group, each of which may be substituted one or more times by the same or different substituents such as fluorine, gas, bromine, sulfhydryl, trifluoromethyl, -COR11 and/or sulfonylamino. R is more preferably a gas or a CrC^ which is substituted one or more times by the same or different substituents of the same or different fluoro, gas, mercapto, decyloxy, ethoxy, decylcarbonyloxy and/or fluorenyl groups. An alkyl group; or a cyclopropyl fluorenyl group or a QC: 7-cycloalkyl group substituted with one or more substituents, such as the same or different gas, mercapto or trifluoromethyl, as desired; or a strepyl, benzyl group , 丨 phenethyl, 2-phenethyl or 2 fluorenyl-2-phenylethyl, each of which may be the same or different fluorine, gas, bromine, sulfhydryl, trifluoromethyl, _c〇Rll and / or a substituent such as a repeating amine group is substituted one to three times.

Rl is very preferably hydrogen, decyl, ethyl, n-propyl, isopropyl, 2,2-fluoroethyl or 2,2,2-difluoroethyl, or cyclopropyl or cyclohexyl, each R1 and R10 are more preferred as a sulfhydryl group by a substituent such as a gas, a mercapto group or a trifluoromethyl group. ° The site is preferably hydrogen, r2, R3, r4, r5, r6, r7, r^r9, which are each independently a phenyl group or a phenyl group. 6

S 201200017 R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, n-, iso-, second- or Tri-butyl. If X is an anion, X is preferably chlorine. If ruthenium is a cation, 乂 is preferably 11+, 八§+彳62+,]^112+ or 2112+. If X is a cation, X is more preferably Ag+, Mn2+ or Zn2+. R1G is preferably hydrogen, decyl, ethyl, methylcarbonyl or ethylcarbonyl, or is optionally substituted by a substituent such as fluorine, chlorine, sulfhydryl, ethyl, n-propyl, isopropyl or trifluoromethyl. Or multiple times of phenyl. R1() is more preferably hydrogen, fluorenyl or fluorenylcarbonyl or phenyl. R11 is preferably a hydroxyl group, a mercapto group, an ethyl group, a methoxy group or an ethoxy group. R11 is more preferably a hydroxyl group or a decyloxy group. Specifically, the compounds described in the Preparation Examples are referred to. More specifically, it may be preferable to use the compound of formula (la) R6 R5,

Where m is 1, η is the ionic charge of X, X is an anion selected from the group consisting of cr or ruthenium, and R1 to R9 have the general, preferred, better, etc. definitions indicated above. The novelty in this specification is the maleidinium salt of the following formula (IV) (IV) (IV) 20110017

In the middle

Rla is hydrogen; or a CrC8-alkyl group substituted one or more times by the same or different halogen, -R10a and/or -CORlla substituents; a clothing base or a C3_C7_cycloalkyl-Ci-C2 - the base of the 'respectively substituted one or more times with the same or different substituents such as halogen, CrC4-alkyl or CrCr haloalkyl; or aryl, aryl-(CrC4_alkyl) or arylsulfonate Amine groups, each of which is optionally substituted one or more times by a substituent such as the same or different dentin, CrC4-alkyl, CrCr il alkyl, -CORlla or sulfonylamino group, R2a, R3a, R4a, R5a, R6a, R7a, R8a and R9a are, independently of each other, murine, crcv alkyl, or phenyl or benzyl, each optionally being the same or different halogen, CrC4_alkyl, CrC4-alkoxy or crc4- The thiopurine substituent is substituted one or more times, wherein if Rla is hydrogen, methyl, hydroxydecyl, methylcarbonyloxyindenyl, chloroindenyl, benzyl, stupyl or methoxymethyl, and Xa is qi , R3a, R3a and R5a are not hydrogen at the same time, R is hydrogen, C]-C4_alkyl, Ci_C4_pyringyl, or optionally halogen, C1-C4-hoth or C1-C4-halogen Substituting a substituent such as a burn group The multiple aryl,

Rlla is a hydroxyl group, a CrC4-alkyl group or a CrC4-alkoxy group.

S 201200017 is 1, η is the ionic charge of χ3, and χ3 is an anion selected from cr or Br-. Here, R 丨 1 RHa and 乂 3 have the preferred, better, very much the same as described above for the corresponding groups, and the above compounds are further excluded. . In the other case of the invention, the compound (b) compound R\ 0

N Corpse - R4 V-R3 Ο (lb) where R to R have the general, preferred, better definitions of the above indications. The novelty in this specification is a maleidinium salt of the following formula (V).

Wherein lb/·*- R is hydrogen; or Ci_C8_alkyl substituted one or more times by the same or different substituents such as halogen, _ORi〇b and/or -CORllb; CrCr·cycloalkyl or VCV cycloalkyl-CrCr alkyl groups, each of which may be substituted one or more times by the same or different substituents such as halogen 'h-Cr alkyl or haloalkyl; or aryl or aryl (Ci_c4_alkyl) Or an arylsulfonylamine group, each of which is optionally substituted by the same or a substituent of 201200017 different halogen, CrC4-alkyl, (^-(: 4-haloalkyl, -CORllb or sulfonylamino) in the aryl moiety One or more times, R2b, R3b, R4b and R5b are independently of each other hydrogen, CrC6-alkyl, or phenyl or benzyl, each optionally being the same or different halogen, CrC4-alkyl, CVC4-alkoxy Or a substituent such as CrC4-alkylthio is substituted one or more times, wherein if R]b is hydrogen, fluorenyl, hydroxyindenyl, fluorenylcarbonyloxyindenyl, chloroindenyl, benzyl, phenyl or oxime In the thiol group, R2b, R3b, R4b and R5b are not hydrogen at the same time, R1Qb is hydrogen, C丨-C4-alkyl, CrC4-alkylcarbonyl, or optionally ii, CrC4-alkyl or CrC4-haloalkyl Substituting a substituent for one or more ,

Rllb is a hydroxyl group, a CrC4-alkyl group or a CrC4-alkoxy group. Further, here, 11115 to R5b, R1()b and R11b have the preferred, better, very preferred, and the like defined above with respect to the corresponding groups of R1 to R5, R1Q and R11; outer. In another embodiment of the invention, it is possible to preferentially use a compound of the formula (Ic) below.

(2/n X)m

Where m is 1, η is the ionic charge of X, and X is a cation selected from the group consisting of Η+, Ag+, Co2+, Cu2+, Fe2+, Mn2+, Ni2+, Pd2+, and Zn2+, and 201200017 R1 has the general indications above, Better, better, etc. In the compound of the formula (1) or (Ic), if X is h+, fluorenyl SH is obtained in each case. The novelty in this specification is the maleidinium salt of the following formula (VI).

In the middle

Rle is hydrogen; or a CrC8-alkyl group which is substituted one or more times by a substituent such as the same or different halogen, _Ri〇c and/or -CORlle, as needed; Q-CV cycloalkyl or c3-C7-ring Alkyl-crC2-alkyl, each optionally substituted one or more times by substituents such as the same or different halogen, crc4-alkyl or crc4-i alkyl; or aryl, aryl-(CrC4-alkyl) Or an arylsulfonylamine group, each of which is optionally substituted one or more times with an aryl moiety by a substituent such as the same or different halogen, Crc4-alkyl, crC4-alkyl, _C〇Rllc or scutane , R10c is 氲, CA·alkyl, Cl_C4_, or, if necessary, substituted by a substituent such as a hydroxyl, CrC4_alkyl or CrC4-decyl group, or an aryl group, R is a super group, C1- C4-alkyl or Ci-C4-alkoxy, m is 1' η is the ionic charge of Xe, and

Xc is a cation selected from the group consisting of Ag+, C〇2+, Cu2+, Fe2+, 2+, from +, pd2+ and Zn2+, wherein if Rlc is hydrogen, methyl, methyl, 201200017 phenyl or methoxymethyl, Methylcarbonyloxymethyl, gas methyl, benzyl, then xe is not Ag+. Further, here, Rlc, Rl°e, Rile, R and X (known ion) groups, R and Xe and η have the above-mentioned preferred groups for the corresponding groups, and further exclude the aforementioned compounds outer. R1, R10, R1丨盥χ meet her ^, better, very better, etc.; /, formula (1) and formula (la), (lb), (IV) and (v) Malay Among the imine salts, urea-substituents can occur in two different isomeric forms, and are particularly remarkable in the case where r9 is a different substituent:

For the sake of brevity, only one possible form is shown in each case. All of the maleimide salts of the formula (I) which may be used in accordance with the invention may optionally be present in the form of a polymer, especially a maleimide salt of the formula (Ic) in the form of a diindenyl group. The maleidinium salt of the formula (I) which can be used according to the present invention can be produced by a known method (refer to CTzem. 1967, 7(10), 1559-1570). For example, in the first stage, a maleimine of the formula (VII) is reacted with a thiourea of (VIII) and (IX) in a non-aqueous solvent to obtain a maleic imide salt of the formula (1); Weakly alkaline hydrolysis to obtain a salt-like compound of formula (II); in a solution of ammonia, a precipitation reaction of a metal salt with a compound of formula (II) or (III) may alternatively produce a malayan formula of formula (III) Amine salts.

S 201200017

Fine-grained ▲ This invention relates to the protection of crops used to control harmful fungi. The mashing, and the composition containing at least one maleic imide salt of the formula (1) is preferably a fungicidal composition containing an agricultural adjuvant, a solvent, a carrier, an interfacial active substance or an increase Filling. Further, the present invention relates to a method for secretly controlling a microbial microorganism, and according to the present invention, a maleic imide salt of the formula (1) is transported to a phytopathogenic fungus and/or a habitat thereof. According to the present invention, "carrier" means a compound or organic or inorganic substance which is combined or mixed with an active ingredient for easier application (including application to plants or ageing bodies or seeds); Solid or liquid, usually inert and suitable for agricultural use. The solid or liquid of the ugly genus is: for example, the salt and finely ground natural 13 201200017 minerals such as kaolin, clay, talcum powder, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and fine Grinding synthetic minerals, such as finely cut stone stone, oxidized and natural or synthetic stone acid, resin, woven, solid fertilizer, water, alcohols (especially butanol), organic solvents, mineral oil and Vegetable oils and their derivatives. Mixtures of such carriers can also be used. Suitable solid carriers for granules are, for example, crushed and classified natural minerals such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic coarse powders, and organic materials, For example, granules, coconut shells, ear of corn and tobacco stalks. Suitable liquefied gas extenders or carriers are liquids which are gaseous at ambient temperature and atmospheric pressure, such as aerosol propellants, such as halogenated hydrocarbons, and butane, propane, nitrogen and carbon dioxide. Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as argan = gum, polyvinyl alcohol, polyvinyl acetate or natural phospholipids, may be employed in the formulation. Classes such as brain fats and egg filling and synthetic shafts. Others may add mineral oil and vegetable oil. It is also possible to use, for example, an organic auxiliary solvent if the hydrazine used is water. Essentially suitable liquid solvents are: aromatic compounds, tender: f toluene, methyl or benzonaphthalene; gasified aromatic compounds or gasified aliphatic hydrocarbons, such as chlorobenzenes, chloroethanes, etc. Wei smoke, such as mine with & 'W smoke', ,. ^, broad oil fraction, mineral oil and plants such as butanol or glycol such as fine 'methyl isobutyl shrine ring 1 201200017 steep / combined with, for example, dimethyl hydrazine and two, Β _ hurricane; and water. The composition according to the present invention may contain the following examples, such as an interface active material. Appropriate: the step-in-step ingredients, and/or the foaming agent, the ionic or sexual substance as the emulsifier aerosol, or the dispersing agent or the acidity of the interfacial active substance. An example of a polyacrylic acid salt, a lignosulfonate salt, a sulfonate and a fatty alcohol or a polycondensate of a fatty acid or a lipid heart and an oxygen atom 1 this type (preferably minus silk _ or aryl stupid _ acid = salt, bovine acid derivative (preferably burnt cow's plum), poly = base alcohol benzene Benz's miscellaneous purpose, plural Alcoholic acid, and derivatives of compounds containing sulfate, various roots and two roots, such as aryl aryl ethane, 妓 §, sulphur _, aryl sulphate _, protein hydrolysate, Wood sulfite waste liquid and mercapto cellulose. If the active compound and/or its inert (IV) are soluble in water and the application occurs in water, the presence of the interface active substance is necessary. Between the percentage of 5盥4丄 of the composition according to the invention, a coloring agent such as an inorganic pigment such as iron oxide may be used in the interior. Huachin, Prussian Blue, and organic materials such as alizarin dyes, azo dyes and gold brains, and micronutrients such as iron bells, boron, copper, indium, zinc and zinc salts Other additives may also be present when appropriate, such as protective body, adhesives, adhesives, thickeners, shake-reducing substances, penetrants, fixatives, chelating agents, complex forming agents. For example, active in combination: 201200017 can be combined with any solid or liquid additive conventionally used for formulation purposes. Typically, the formulation contains between 0.05 and 99% by weight, between 0.01 and 98% by weight, preferably Between 0.1 and 95% by weight, particularly preferably between 0.5 and 90% by weight, very preferably between 10 and 70% by weight of active compound. The active compound or composition according to the invention may be used as such, or Depending on their respective physical and/or chemical properties, they may be used in the formulation or in the form in which they are prepared, such as aerosols, capsule suspensions, cold mist concentrates, warm mist concentrates, encapsulated granules, fine Granules, seed treatment with a thick flow Shrinkage, ready-made solution, dispersible powder, emulsifiable concentrate, oil-in-water emulsion, water-in-oil emulsion, large granule, granule, oil dispersible powder, oil miscible flow concentrate, oil miscible Liquid, vesicles, pastes, seeds coated with pesticides, suspension concentrates, suspension emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, powders and granules, water-soluble granules Or lozenges, water-soluble powders for seed treatment, wettable powders, natural products and synthetic materials impregnated with active compounds, microencapsulation in polymeric and seed coatings, and ULV cold mist and warm mist formulations. The formulations may be prepared by methods known per se, for example, by bringing the active compound together with at least one conventional extender, solvent or diluent, emulsifier, dispersing agent and/or binder or fixative, wetting agent, water repellent, when appropriate Desiccant and UV stabilizer and, where appropriate, dyes and pigments, defoamers, preservatives, auxiliary thickeners, adhesives, gibberellin and further

S 16 201200017 Step processing aid mixing. Compositions in accordance with the present invention include not only ready-to-use formulations that can be applied to plants or seeds in a suitable device, but also commercial concentrates that must be diluted with water prior to use. The active compounds according to the invention may be as such or in the form of (commercially available) formulations and in such formulations as, for example, insecticides, attractants, sterilants, bactericides, acaricides, nematicides, The use forms of the preparation of mixtures of fungicides, growth regulators, herbicides, fertilizers, protectants or other (known) active compounds of semiochemicals appear. Treatment of plants and parts of plant systems with active compounds or compositions according to the invention is carried out directly or using conventional treatment methods such as impregnation, spraying, atomizing, rinsing, evaporation, dusting, fogging, Spreading, foaming, lacquering, coating, soaking, dripping and rinsing; in the case of propagation materials (especially seeds), further use of dry seed, wet seed treatment, slurry treatment, skin formation, coating One or more coatings or the like act on their surroundings, habitats or storage spaces. Further, the active compound may be applied by an ultra-low volume method, or the active compound preparation or the active compound itself may be injected into the soil. Further, the present invention also includes a method of treating seeds. The invention further relates to seeds that have been treated according to one of the methods described in the previous section. The seed according to the present invention is used in a method for protecting a seed against a harmful fungus. Herein, seeds treated with at least one active compound according to the invention are used. 201200017 2 The active compound or (four) according to the invention is also prepared in the treatment of species. The most harmful damage to the crop plant caused by the pest is caused by the heart = during storage or after sowing, and during the germination of the plant or the germination of f . This stage is particularly critical because the growth of plants, mites and young ones is particularly sensitive, and even small injuries can cause plant deaths. Therefore, the use of appropriate compositions to protect seeds and germinated plants has received great attention. The ancient station has long been known in the industry [by knowing how to treat plant seeds to control pathogenicity. However, there is a problem with the treatment of seeds that cannot be resolved in a satisfactory manner by a series of cranes. Therefore, the period of development is to develop a method for protecting seeds and germinating plants after cropping or after germination of plants; 2 the amount of active compound used is optimized, and the seeds are provided with π:, rush Maximum protection from phytopathogenic fungi, only the active compound does not harm the plant itself. In particular, the method for treatment also has to take into account the inherent fungicidal properties of the genetically transformed plant, and to achieve the seed under the crop protection composition. Therefore, the present invention also relates to the use of the composition of the present invention, In order to protect seed and germinating plants from phytopathogenic fungi, the use of the composition according to the present invention to protect seeds and germinating plants against phytopathogenic money is further related to the present invention. The invention group is directed against seeds of phytopathogenic fungi. Λ保遴's control of the 201200017 crop-derived fungi was mainly carried out with concerns about crop protection === points. Because of the impact, the industry is committed to reducing the possibility of giving, animal health. One of the advantages of this invention is that! . Or the specific infiltration properties of the composition, the seed treated with the active compound of the tree not only protects the seed-specific active compound or composition from the invasion of the phytopathogenic fungus; the plant produced after germination or the immediate treatment of the crop . It can be exempted from being considered as an advantage when planting. It can also be used as a compound or a plant for the growth of a compound or a group of plants capable of exhibiting resistance: the seed or the active compound or composition of the present invention. Where =: = It: According to the performance of, for example, insecticidal protein, can be hunt, and further increase can be observed. Surprising the effectiveness of the invasion.额外Additional increase in defenses 4 円 Composition of the invention to protect agriculture, greenhouses, forests, gardens, seeds of any plant species used in cultivation; = = Valley of sub-forms _ such as wheat, large seeds: Benan粱/millet and oats), corn, cotton j-a peanut, 4 (2 such as sugar beet and copper beet), vegetables (such as sage, courgette = Yucao, (see also) heart) The ornamental plants should be treated as seeds of Yi (such as wheat, barley, bare 201200017 wheat, black wheat and oats), corn and rice. It is also of particular importance to treat a gene-transferred seed with an active compound or composition according to the invention as described below; this refers to a seed containing a plant which permits at least one heterologous gene of a polypeptide or protein having insecticidal properties. . The heterologous gene in the gene-transferred seed can be derived, for example, from Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Corynebacterium. Microorganisms of species such as Clavibacter, Gl〇mus or Gliocladium. Preferably, the heterologous gene is derived from the genus Bacillus and has a gene product that is active against European corn borer and/or western corn rootworm. A particularly good one is a heterologous gene derived from Bacillus thuringiensis. In the present specification, the composition according to the present invention is applied to the seed in its own right or in a suitable formulation. Preferably, the seed is stabilized without causing any damage to the treatment to be disposed of. In general, seeds can be processed at any point between harvesting and sowing. The seeds used have usually been isolated from plants and are not contaminated with cobs, shells, stems, skin, hair or pulp. Therefore, it is possible to use, for example, a seed which is collected, dried, branched, and dried to a moisture content of 15% by weight or less. Alternatively, it is also possible to use a seed which has been dried, for example, treated with water, and then dried. When the seed is treated, care must be taken to ensure that the amount of the composition according to the invention applied to the seed and/or the amount of the further additive selected does not adversely affect seed germination, or that the resulting plant is not injurious. = Don't be an active compound with a phytotoxic effect at a specific rate of application 201200017 In particular, this must be kept in mind. The composition according to the invention can be applied directly, i.e. without further ingredients and undiluted. In general, it is preferred to apply the composition in the form of a suitable formulation to the seed. Suitable formulations and methods for treating seeds are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A ' US 2003/ WO 196/080675 A, WO 2002/028186 A2. The active compounds which can be used in the present invention can be converted into conventional seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating materials for seed, and ULV formulations. These formulations are prepared by known methods to admix the active compound with conventional additives such as, for example, conventional extenders and solvents or diluents, colorants, wetting agents, dispersing agents, emulsifiers, defoamers Preservatives, auxiliary thickeners, adhesives, gibberellins and water. Desiccants which may be present in the seed dressing formulations which may be used in the present invention are all known colorants for such use. Both water-insoluble pigments and water-soluble dyes can be used; examples of coloring agents that can be mentioned are known as Rhodamin B, C.I_pigment red 丄j2 and C_I · Solvent red No. 1. The wetting agent which can be used in the preparation of the seed dressing product which can be used in the present invention is any one which is conventionally used for formulating agrochemically active compounds and for promoting the second wetness; the alkylnaphthalenesulfonate can be preferably used. For example, 201200017 diisopropyl- or diisobutylnaphthalenesulfonate. Suitable dispersing agents and/or emulsifiers which may be present in the seed dressing formulations which may be used in the present invention are all nonionic, anionic and cationic dispersing agents which are conventionally used for the formulation of agrochemically active compounds; A nonionic or anionic dispersant or a mixture of a nonionic and anionic dispersant is used. In particular, suitable nonionic dispersants which may be mentioned are ethylene oxide/propylene oxide block copolymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, And their acidified or sulfated derivatives. In particular, suitable anionic dispersants are lignosulfonates, polyacrylates and arylsulfonate/furfural condensates. Defoamers which may be present in the seed dressing formulations which may be used in the present invention are all suds suppressing materials which are conventionally used for the formulation of agrochemically active compounds; the use of a sulphate defoamer and stearic acid may be preferred. Preservatives which may be present in the seed dressing formulations which may be used in the present invention are all materials which can be used in the agrochemical compositions for such use; examples which may be mentioned are dichlorophenol and benzyl alcohol hemiformal. Auxiliary thickeners which may be present in the seed dressing formulations which may be used in the present invention are all materials which can be used in such agrochemical compositions for such use; cellulose derivatives, propionic acid derivatives, xanthan gum Modified clay and highly dispersed vermiculite are more appropriate. Adhesives which may be present in the seed dressing formulations which may be used in the present invention are all conventional binders which can be used in seed dressing products; preferred embodiments are polyvinyl σpyrrolidine, poly Ethyl acetate, polyethylene

S 22 201200017 Alcohol and tylose. The gibberellin which may be present in the seed dressing formulation which may be used in the present invention is preferably gibberellin A1, A3 (=gibberellic acid), A4 and A7; particularly preferably gibberellic acid. Gibberellin is a known compound (see R. Wegler " Chemie der Pflanzenschutz- und

Schadlingsbekampfungsmittel "[Chemicals of Plant Protection Agents and Pesticides], vol. 2, Springer Verlag, 1970, p. 401-412). The seed dressing product formulation useful in the present invention can be used to treat a wide range of seeds, including seeds of genetically transformed plants, directly or in advance after dilution with water; in this case, it is also possible to interact with the substance forming the expression. And additional synergies occur. Suitable devices which can be used to treat seeds with a seed dressing formulation which can be used in accordance with the invention or a formulation prepared by the addition of water are all mixing devices which are generally available for application to the seed. In particular, the seed is placed in a mixer and then subjected to a seed application procedure, adding the desired amount of seed dressing product formulation in each case (added as such or added before dilution with water) to make it in the mixer The contents are mixed until the formulation is evenly distributed on the seed; if appropriate, the drying step is followed. The active compound or composition according to the invention has a strong fungicidal activity' which can be used to control harmful fungi on crop protection and material protection. The maleic imide salts according to the present invention can be used for crop protection to control piasmodiophoromycetes, Oomycetes, chytridiomycetes, Zygomycetes, ascomycetes. Ascomycetes, Basidiomycetes 23 201200017 (Basidiomycetes) and Semi-known g-class (1) _ legs are called (2) (four). The killing agent according to the present invention can be used therapeutically or prophylactically for controlling Phytophthora®. Accordingly, the present invention is also a method for the therapeutic and prophylactic control of phytopathogenic fungi by applying the active compound or composition according to the present invention to soils grown on seeds, plants or parts of plants, fruits or plants. The compositions according to the invention for controlling phytopathogenic fungi on plant protection contain an effective, but phytotoxic amount of the active compound according to the invention. By "effective, but no phytotoxic amount" is meant an amount of a composition according to the invention sufficient to adequately control or completely eradicate the fungal disease of the plant without causing significant phytotoxic symptoms. In general, this rate of application may vary over a relatively wide range; depending on, for example, the fungi, plant, climatic conditions, and composition of the composition according to the present invention. The treatment of plant aerial parts, plant propagation material and seeds, and soil is permitted due to the good plant tolerance of the active compounds at the concentrations required to control plant diseases. All plants and parts of plants can be treated in accordance with the invention. In the present specification, a plant is understood to mean all plants and plant communities, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants obtainable using conventional breeding and optimization methods or using biotechnology and recombinant methods or a combination of such methods, including genetically modified plants and plant varieties including or not protected by plant breeders. Some plants are to be understood as meaning plants

S 201200017 Free: With underground parts and organs, such as seedlings, s, flowers and roots, examples can be described as leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and roots, tubers and rhizomes. Some plants also include harvested materials and asexual and sexually propagated materials such as cuttings, tubers, rhizomes, cuttings and seeds. The active compound according to the invention is suitable for protecting plants and plant organs, increasing the yield, improving the quality of harvested crops, having good plant tolerance, having beneficial toxicity to various warm-blooded animals, and being harmless to the ecological ring brother. It is preferably used as a crop protection composition; and is active against general sensation and resistant lines and all or each developmental stage. Plants which can be treated according to the invention are as follows: cotton, flax vines, fruits, blasts, such as Rosaceae (and osflcefle) plants (such as pome fruits such as apples and pears, and stone fruits such as apricots, cherries) , almonds and peaches, and soft fruits such as strawberries), families, walnuts, sand plants, birch (such as coronation, lacquer (10) plants, Fagaceae (7^ inhibit Ceae) plants, Moraceae (Moraceae) Plant, Oleaceae, Actinidia, Zymphaceae (Z(10) plant, Musa (eg banana and banana), Rubidaceae CRwMflceae) (eg coffee), Camellia, Sycamore SYercw"ac(10)e) , Rutaceae (and wMceae) plants (eg, scorpion, willow and grapefruit); % (So/awaceae) plants (eg, Fanyou), Liliaceae, Aieroceae (eg lettuce), pay X. (t/m heart / / (/ 'erae) plants, Owcferae plant (201200017), carp (10)) plants, germination, batches, "Cal (10) plants (such as cucumber), onion 〇 4 ///(3ceae) plants (eg leek, ocean) ), butterfly flower family CPfl; ?z7z · (10) acefle) plants (such as peas); major crop plants such as grasses (<^wz'w_) plants (such as corn, turf, cereals such as wheat, rye, rice, barley) , oats, sorghum, millet and triticale), Compositae (eg sunflower), cruciferous (7) plants (eg white cabbage, purple cabbage, broccoli, broccoli, Brussels sprouts, cabbage, broccoli, Xiaoluo, And m dishes, horseradish and water buds), foot (fine alpha (four)) plants (such as beans, peanuts), butterfly-shaped plants (eg = ugly), pain plants (such as horse bells), medicine plants ( For example, beet, mining, Swiss silk, beetroot); useful plants of the court and forest towels, ornamental plants; and their _ in each case, the eight plants have been described as 'according to the invention a plant product obtained by a biological breeding method (for example, hybrid or native ' '' plastid merging) (4) a plant, and a part thereof, in the case of a cultivating method, using a recombinant method, Through genetic transfer plants and plant varieties (base 2: specialized system Binding eligible plant "part" or "parts of plants soil & Biological), and the lower part in each case commercially available or in the use of" special frieze: described in the above. According to the invention, the filament is used. Plant 2 plants are particularly preferred for root breeding, utilization of mutations or the use of two senses to mean plants that have utilized the characteristics; they may be variants and = technically developed in novel form. Species, biotypes and genotypes

26 201200017 (The treatment method of GM^f can be used to treat genetically modified organisms), such as plants or seeds. A genetically modified plant (or a gene-transplanted plant) is a plant in a human genome. A "heterologous gene" is a nuclear sputum, i means a gene that is provided or assembled outside the plant, and is introduced into the polypeptide or Obtaining I, steroid or mitochondrial genome by expressing the protein of interest or use case 1 'shame' to down-regulate or suppress other genes present in the plant, thief + a technique, co-suppression technique or RNA interference -RNAi technology in the genus or enhances his nature. The til in the genomic body; also known as the transgenic gene, which is caused by the translocation of the plant in the plant due to the translocation or basal climatic; plant variety, its location And the growth conditions (soil, super-increasing (s"tr) mosquito's treatment of the invention of the county can also produce the actual expected I"). Therefore, for example, it may occur beyond the German fruit: silk rate reduction and / Or live (4) 11 enlargement and / / active compound and composition activity increase 乂 2 length is better, resistance to high temperature or low temperature is increased, tolerance to drought, soil moisture content is increased, flowering is much easier, easy to harvest , color fruit cautiously turned into a product of better quality and / or nutritional price The value is higher than the concentration of the sugar in the second pass, the storage stability of the harvest product and the specific application rate, and the plant is also potently effective. Therefore, the composition U is suitable for mobilizing the plant defense 201200017 system' In order to combat the attack of harmful phytopathogenic fungi and/or microorganisms and/or viruses. If appropriate, this may be one of the reasons for the enhancement of the activity (for example against fungi) of the composition according to the invention. In the present specification, plant-enhanced (Resistance-induced) substances are to be understood as meaning also stimulating the plant defense system. When the subsequent inoculation of harmful plant pathogenic fungi, the treated plants exhibit a considerable degree of resistance to their harmful plant pathogenic fungi. The substance or composition thereof. Therefore, the substance according to the present invention can be used to protect plants against the attack of the above pathogenic bacteria during a specific period after the treatment. The period of validity is usually 1 to 10 days after the plant is treated with the active compound. Preferably, it is from 1 to 7 days. Plants and plant varieties that are preferentially treated in accordance with the present invention include those that are given to them (whether utilizing And/or biotechnological method obtainers) all plants of genetic material of particularly advantageous and useful properties. Plants and plant varieties which are preferably treated according to the invention are also resistant to one or the same biological stress, ie Animals and microorganisms: for example, having better defense against nematodes, insects, cocoons, phytopathogenic fungi, bacteria, viruses and/or viroids. Plants and plant varieties which may also be treated according to the invention are one or more Abiotics are resistant to their plants. Abiotic stress conditions can include, for example, drought, low temperature exposure, heat exposure, osmotic stress, water immersion, increased soil salinity, increased pre-exposure, ozone exposure, glare Exposure, nitrogen nutrient limitation, 4 nutrient limitation or avoidance of shading. Plants and plant varieties which may also be treated according to the invention are plants having yield-increasing properties. The increase in production of these plants may be due to,

S 201200017 For example, improved plant physiology, growth and development, such as water use efficiency, water holding efficiency, enhanced nitrogen use, enhanced carbon assimilation, enhanced photosynthesis, increased germination efficiency and accelerated maturity. Furthermore, yield can be affected by enhanced plant structure (under adverse and stress-free conditions), including early flowering, flowering control of hybrid seeds, seedling vigor, plant size, internode number and distance, root growth, seed size, Fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed quality, increased seed filling, reduced seed spreading, reduced pod splitting and lodging resistance. Further yield characteristics include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, processability enhancement, and storage stability. Plants which can be treated according to the invention are hybrids which have demonstrated hybridization advantages, or heterozygous/tongue specific characteristics (generally producing higher yield, higher vigor, healthier and better resistance to biotic and abiotic stress factors) plant. Such plants are typically produced by crossing inbred male/sterile parental lines (female parental) with another inbred mating male_fertile parental line (male parental). Hybrid seeds are typically harvested from male plants and sold to growers. Male impurities are sometimes (for example, in corn) emasculated (i.e., mechanically removed male reproductive organs or male flowers) to produce the result of a genetic determinant of the 'generally more' male genital plant. Under the shape of Yusaki, especially when the seeds are lightly harvested from the hybrid plants, it is useful to ensure that the male plants can be fully recovered from the plant towels containing the exclusive money. This is achieved by ensuring that the male parent has a suitable sputum recovery gene that restores the male circumstance in the hybrid plant 201200017 containing the responsible male determinant. The genetic determinant of male sex may be located in the cytoplasm; examples of cytoplasmic and male convulsion (CMS) are exemplified by the Brassica plant. However, the genetic determinant of male sex can also be located in the nuclear genome. Male plants can also use plant biotechnology methods such as genetics

The method is obtained. A particularly useful method for obtaining an amaryl plant is described in WO 89/10396, wherein, for example, a ribonuclease such as a ribonuclease is selectively expressed in the cells of the stamens of the stamens; thus it can be utilized in A ribonuclease inhibitor such as barstar is found in the tapetum cells to restore sputum. A plant or plant cultivar (obtained using plant biotechnology methods such as genetic engineering methods) which can be treated according to the invention is a herbicide tolerant plant, even if it is resistant to one or more specific herbicides. Such plants can be obtained by gene transformation or by selecting plants containing mutations conferring tolerance to such herbicides. The herbicide-tolerant plant is, for example, a glyph〇sate-tolerant plant, even if it is resistant to the herbicide galamin or its salt. For example, a galaxin-resistant plant can be obtained by using a transformant plant encoding an enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the coding genes of the AroA gene (mutant CT7) of A. typhimurium, the CP4 gene of Agrobacterium#_), the morning glory jgpsps, the genus EPSPS, or the genus EPSPS. It can also be an EPSPS. The Jiaphos-tolerant plant can be obtained by using the gene encoding the phosphorylation oxidative 201200017 reductase; and can be obtained by using the gene encoding the gamma-stained transferase enzyme; and the mutation containing the above-mentioned gene can also be selected. Plants are obtained. ^Other herbicide-tolerant plants are, for example, herbicides such as bialaph〇s, phosphinothricin or chlorpyrifos (for their inhibitory enzymes). Gluf〇sinate)] with patience "^ two things. Such plants can be obtained by expressing an enzyme that detoxifies the herbicide or a mutant face-faced amine indoleamine synthase enzyme that is resistant to the action. An effective detoxifying enzyme is, for example, a material encoding a secondary scutellaria bait transferase [eg, a bar or pat protein derived from Strept〇my, ces species]; For the table flavonoids B to _ domain. π human spleen sputum-step herbicide-tolerant plants are also resistant to herbicides that inhibit the fermentation of ferric pyruvic acid dioxin _ qing _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ . An inhibitor II = a gene that is visualized by the naturally occurring coding-resistant HppD value as the HPPD enzyme. The permanent coding mutation of HITPD can also be used regardless of the tolerance of HPPD 丨 w inhibitor 〇 inhibitor to natural HppD yeast to form urinary black (tetra) tyrosine transesterification, plant resistance to HPPD inhibitor = plant pay. The enzyme-encoding gene plus Hppn 4 is promoted by the dehydrogenation of the enzyme pre-benzoic acid.咖耐转(四)码基_植物进行与amp; Acid Lactic Acid Synthetase The herbicide-tolerant plant is a plant that is resistant to the 31 201200017 (ALS) inhibitor. Known ALS inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidine, pyrimidinyloxy(thio)benzoate, and/or sulfonylamine carbonyl triazolinone weeding Agent. It is known that various mutations of the ALS enzyme (also known as acetamidine synthase, AHAS) t confer tolerance to different herbicides and various group herbicides. The manufacture of sulfonium-urea-tolerant plants and imidazolinone-tolerant plants has been described in International Publication WO 1996/033270. Further sulfonamide- and imidazolinone-tolerant plants are also described, for example, in WO 2007/024782. Other plants which are resistant to imidazolinone and/or sulfonium urea can be obtained by using an inducing mutation, selecting it in cell culture in the presence of a herbicide, or using mutation breeding. Plants or plant varieties (obtained using plant biotechnology methods such as genetic engineering methods) which can also be treated according to the invention are insect-tolerant gene-transgenic plants' even plants which are resistant to invasion by specific target insects. Such plants can be obtained by gene transformation or by selection of plants containing mutations conferring resistance to such insects. In the present specification, the term "insect tolerance gene transfer plant" includes any plant containing at least one transgene consisting of a coding sequence encoding a protein: 1) an insecticidal crystal protein derived from Suri or its Insecticidal parts, such as the insecticidal crystal proteins listed on the following website: http.//www.lifesci. Sussex.ac.uk/Home/Neil_Crickmore/Bt/ or its I-parts' such as Cryl Ab, CrylAc, CrylF, Cry2Ab,

a Cry protein such as Cry3Ae or Cry3Bb or an insecticidal part thereof 201200017; or 2) a crystal derived from S. cerevisiae having insecticidal activity in the presence of a second other crystal protein or a part thereof derived from S. cerevisiae An egg from or part thereof, such as a binary toxin composed of Cy34 and Cy35 crystal proteins; 'or 3) a hybrid insecticidal protein consisting of two different insecticidal crystal protein fractions derived from S. cerevisiae, such as the above 丨) protein a hybrid or a hybrid of the above 2) protein, for example, a CrylA.105 protein produced by the corn case M〇N98〇34 (w〇2007/027777); or 4) a protein of any of the above 1) to 3) a number of (especially to 10) amino acids have been replaced by another amino acid and/or have higher insecticidal activity against the target insect species due to changes introduced into the coding DNA during transfection or transformation. And/or expand the range of insect species affected by the target 'for example Cry3Bbl protein in maize case MON863 or MON88017, or Cry3A protein in maize case MIR604; 5) from Suri or Cactus (5acz7/ws cerews) Secreted protein Its insecticidal part, for example: http://www.lifesci.sussex.ac.Uk/Home/Neil_Crickmore/Bt/v ip.html listed plant insecticidal (VIP) proteins, such as those obtained from the VIP3Aa protein Protein; or 6) a secreted protein derived from S. cerevisiae or Cactus bacillus in the presence of a second secreted protein from S. cerevisiae or Cactus bacillus, such as a VIP1A and VIP2A protein. a metatoxin; 7) a hybrid insecticidal protein consisting of a different secretory protein fraction derived from S. cerevisiae or Cactus bacillus, such as a hybrid of 1) above or a hybrid of 33 201200017 2) protein; 3) any of the proteins 'some of which (especially i to Η)) amino acids have been replaced by other amino acids and/or because of the inducible change in the 阙DNA during transformation (but still encoded whitening) = = higher insecticidal activity against the target worm species, and / or expansion of the range of insect species, such as the cotton case c 〇 T = VIP3Aa protein. Of course, 'the insect resistance base of this article also includes = Any of the above 1 to 8 types of protein-coding gene combinations - In a specific example, 'insect-tolerant plants contain more than one transgene of coding = to class 8 any-like proteins to expand the range of the affected 2 insects, or to kill by the use of the same target Different types of proteins (such as different receptors in the (four) towel, 'combination sites') may be used to delay the development of insect resistance to plants. Plants or plant varieties that may also be treated according to the invention ( It is obtained by using plant biotechnology methods such as genetic engineering methods to be resistant to abiotic stresses. Such plants can be obtained by transforming a gene into a plant or selecting a plant containing a mutation that confers resistance to such a disorder. Particularly useful stress tolerance plants include: a* Plants that contain a transgenic gene that reduces the expression and/or activity of a poly(ADP-ribose) polymerase (PARP) gene in a plant cell or plant; b. Contains plants or plants that reduce it A plant that produces a PARG-encoding gene and/or an activity that enhances the tolerance-resistant transgenic gene; c. contains a niacin-containing indoleamine adenine dinucleotide to remedy the biosynthetic pathway ^ Λ

S 201200017 Plant-Functional Enzymes (including nicotinic glutaminase, nicotinic acid phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide A plant that increases the tolerance-resistant transgenic gene of a synthase or a nicotine guanamine phosphoribosyltransferase). Plants or plant varieties (obtained using plant biotechnology methods such as genetic engineering methods) which may also be treated according to the invention may exhibit altered amounts, quality and/or storage stability of the harvested material and/or altered properties of the particular composition of the harvested material, for example: a genetically modified plant that synthesizes modified starch, which has physicochemical properties (especially amylose content or amylose/amylopectin ratio, branch) compared to starch synthesized in wild type plant cells or plants. The degree, average chain length, side chain distribution, viscosity properties, gel strength, starch granule size, and/or starch granule morphology are altered to make the modified starch more suitable for a particular application. 2) a synthetic non-starch carbohydrate polymer or a genetically transgenic plant having a modified nature without a genetically modified non-starch carbohydrate polymer compared to a wild type plant; an example of which is the production of polyfructose (especially inulin and left) A plant of the glycan type), a plant producing α_1,4 glucan, a plant producing α-1,6 branched α-1,4 glucan, and a plant producing an alternan. 3) Genetically transgenic plants that produce hyaluronic acid. Plants or plant varieties (obtained using plant biological techniques such as genetic engineering methods) which may also be treated according to the invention are plants having altered fiber characteristics, such as cotton plants. Such plants may be obtained by using gene transformation or 201200017 to select plants containing mutations that confer such altered fiber characteristics and include: a) plants containing altered forms of the cellulose synthase gene, such as cotton plants; b) containing altered forms a plant of rsw2 or rsw3 homologous nucleic acid, such as a cotton plant; C) a plant having increased sucrose phosphate synthase expression, such as a cotton plant; d) a plant having increased expression of a sugar synthase, such as a cotton plant; C) an intercellular filament a plant that changes in the gating of a major part of the fiber cell (eg, via a downward regulation of the fiber-selective p_i, 3 glucanase), such as a cotton plant; f) a fiber that has altered reactivity [eg via A plant such as a cotton plant that exhibits an N-acetylglucosamine transferase gene (including nodC) and a chitin synthase gene. Plants or plant varieties (obtained using plant biological techniques such as genetic engineering methods) which may also be treated according to the invention are plants having altered oil performance characteristics, such as canola or related Brassica plants. Such plants can be obtained by genetic transformation or selection of plants containing mutations that confer such altered oil properties and include: ° a) plants that produce oils with high oleic acid content, such as canola plants; b) low yields a plant of a linolenic acid oil, such as a canola plant; ° c) a plant that produces an oil having a low amount of saturated fatty acids, such as a canola plant. 201200017 A particularly useful gene transfer plant that can be treated according to the invention is a genetically modified plant comprising one or more genes encoding one or more toxins and sold under the trade names YIELD GARD® (eg corn, cotton, soybeans) ), KnockOut® (eg corn), BiteGard® (eg corn), BT-Xtra® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton) , NatureGard® (eg corn), Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plants that may be mentioned are corn varieties, cotton varieties and soybean varieties sold under the following trade names: R〇undUp Rea (Jy8 (for Jiaxian plugs, such as corn, cotton, soybeans), Liberty) Link® (resistant to phosphinil buckwheat flavonoids such as canola), (to. imiprazole) and SCS® (resistant to sulfonium, such as corn). Herbicide can be mentioned Sex plants (plants that are resistant to herbicide tolerance breeding by conventional methods) include variants sold under the trade name Clearfield® (eg, corn). Gene-transgenic plants that are particularly useful for treatment according to the present invention contain transformation results, or Plants of the resulting composition, which are listed in the database of various national or regional regulatory agencies (see for example: http://gmoinfo.jrc.it/gmp_browse.aspx and http_//www.agbios.com) /dbase.php) Further, the active compound or composition according to the invention can be used to protect industrial materials against the attack and destruction of harmful microorganisms (for example, 'fungi') in the protection of materials. In the book, 'industrial materials are to be understood as meaning inanimate materials for industrial use. For the purpose of using the active compound according to the invention, 201200017 f is free of the destruction of the coating, the surface, the wallpaper and the wood board, and the spinning is 'for example , Weng Jianjian, paint and plastic sir σ, human, .,, 哉πσ, carpet, leather, wood, other materials: = (4) phase and materials that can be attacked or destroyed by microorganisms are adversely affected Can be subject to, for example, the cooling water loop 2:: for the production of industrial and industrial air conditioning single drive and heating system and ventilation and adhesive agent coating: 2:: [circumference: excellent leather first: ...the material is a slip agent and a heat transfer fluid, · especially good for too _§: wood, paint, cooling, some not = according to salt water or ^ B a a compound according to the invention can be used to protect with buildings, anti-two touch Objects (especially hulls, screens, net products, for control elements) 'to prevent coverage by microbial growth. Guard against inventory. In: the method according to the invention can also be used to protect the goods, store goods Known as meaning a plant or animal derived from a long-term natural source 2 ί:: The original storage of the plant can be protected, for example: force two work = or part of the plant body, such as s, leaves, tubers, two such as pressing or forming ^ (pre) drying, wetting , smashing, grinding, and wood storage goods also include unprotected (such as Jianshiyuan automatic drying and barrier) or finished products (such as furniture). The storage of goods is, for example, animal skin, leather. The active compound of the present invention can prevent some adverse effects, such as rot, discoloration, discoloration or mildew. 38 201200017 Several pathogens of fungal diseases which can be treated according to the present invention can be described as follows (only Not intended to constitute a limitation): From the pathogen of powdery mildew, for example, the species of powdery mildew, for example, and Lu's ' powdery fungus (7) / "(10) coffee Rong ^ ^ ~ (4): fork silk single shell Species, for example, 'such as 'white cross silk single shell (/> 〇 印 / ewcWWc / ^); genus genus, for example, such as Xanthium monofilament shell / / > 2 deduction;; genus H. genus, for example, such as grape fishing silk shell (t / 7? cz > m / a «ecaior) caused by the disease From the rust pathogen, for example, a rust fungus species, for example, such as; Helminthosporium genus, for example, s 'such as P. solani; Plutorius genus, For example, 'such as Phytophthora sojae and P. sylvestris · from); Puccinia genus species, for example, such as Puccinia serrata (Pwccz'm'a rec (10) must (4) or wheat leaf rust Bacteria (Pwcc/mb; Pseudomonas genus species, for example, diseases caused by P. stipitis ([/row less ces appewiZ/cw/ato); by oomycete pathogens, for example For example, the species of the genus Potentillium, for example, a, such as lettuce stalk emblem (price moved / sinking like this); frost genus species, for example, such as Phytophthora (Percwospora or sorrel cream) Mildew (corpse; Phytophthora species, for example, Phytophthora infestans; species of the genus Monotrichum, such as, for example, Plasmopara viticola (corporate / iwmopflra vz'iz.co / fl); Pseudomonas spp., for example, s '如#草假霜霉(Psewi/operc^ospora or Cuban fake cream ΟΡΜί^ορβΓοηίλ^ροΓβΟΜόβπ); Pythium species, for example 39 201200017, The disease caused by the Pythium uhimum bow is, for example, a genus of the genus genus, for example, a genus of the genus Aspergillus sp., or a species of the genus Cercospora, for example, 蓁C. cerevisiae Z>ei/co/a); Cladosporium species, for example, such as melons (C/<3i/os/7〇n'wm cwcwwhhm); Helicobacter sp. Species, for example, such as C. cerevisiae (CocA/ic^o/ws) (conidial type: Drechslera, same: Helminthosporium); For example, the genus Peony is a species of the genus Peony, such as the genus Phytophthora sinensis (circle com'wm; genus of the genus genus, for example, citrus stalks (Ζ > gt ;ζ·αρ〇γ recognition e czYW); Phytophthora species, for example, such as citrus sclerotia 〇E/^>2〇e/flrwceii/i·); Species, for example, G. oeowor/wm / aei/co/or; small genus, such as a small plexus (G/omere"fl; ball A genus of the genus, such as, for example, Staphylococcus aureus Wi/we//z·/); a species of the genus Coriolus, for example, a cancer mold a strain, for example, a mold of the genus Fusarium; a species of the genus Fusarium, for example, a leaf blight of M. crodoc/n'wm m'va/e; a species of the genus Coriolus For example, such as Phytophthora sinensis (M less cosp/?aere//a gram/mco/a) and Fischerella fibrin (M yi; /7e/m\y); Phytophthora species, examples For example, such as wheat leaf blight (P / zaeosp / iaer / iz (10) and rwm); genus genus, for example, such as the nucleus of the genus CP, less ieres); For example, 'Rcmuhria colb-cygni ·, v is a species of genus, for example, 201200017 such as rye 嗓 ^ ^ ^ know like to use ^ ~ this (3) / (4): genus For example, 'such as celery small shell needle spore 叩 _ _ ; ; ; ; ; 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核 核A genus of the genus of the genus Aspergillus, for example, a leaf spot and a leaf blight caused by a black spot of the apple (in the form of a z'waegwa//?); for example, a species of the genus of the genus Such as Coriz'cz'wwgrflfwkearwm; species of the genus Bacillus, for example, such as Fusarium oxysporum (Fw like Www oxyspo) Rwm); the genus of the genus Capsules, for example, such as the top capsule (G^ewm(10)"omyces grflwz'mi); the genus Rhizoctonia, for example, Rhizoctonia solani (and / N_zociom'i3; Rhizoctonia genus species, for example, such as izcw/ormb; Rhizopus sp., for example, as a beaded emblem (TTn'e/av/o/^/s 6iwz' Co/a) caused by diseases of roots and stems; for example, a genus of the genus genus, for example, such as ·???/?.; /avws); Brassica genus, for example, bud-like branches (CVai/os^orz'ww; erionella species, for example, such as ergots (C/flWce/^ Pwrpwrea); Fusarium species, for example, such as Fusarium oxysporum Pw like rz'wm cw/morwm); Gibberella species, for example, such as Gibberella corniculum (Gi from ere/Mzeae); Xanthomonas oryzae, for example, such as Phytophthora sojae (Λ/o(10)mva/b); Phytophthora spp., for example, such as Phyllostachys pubescens (10) Rwm) caused by panicle and panicle disease (including corn cob); by smut fungus, for example, black powder fungus Genus species, for example, 201200017, such as sphaerotheca fuliginea; genus Phytophthora species, for example, wheat sputum smut (77 / / dip 3 cflf Wes), wheat dwarf net Black powder fungus (71·like); black fungus species, for example, such as Helminthosporium occ / ia); black powder i genus species, for example, such as naked black powder bacteria ( [/ you 7 sigh 0 «Μί / β), [/. (10) also caused by the disease; by, for example, the fungus species, such as, for example, Aphis fuliginea; Botrytis species, for example, such as gray Botrytis cinerea c/werefl;); genus of the genus genus, for example, Penici'nium expansum and Penicillium chrysogenum (Pwrpwrog (9) wm); Sclerotinia species, for example, and L'nucleus Phytophthora (Sclerotiniasc/m^/orww); Verticillium species, for example, fruit rot fungus caused by scutellaria (^riz_cz7/z*ww α/όοαίη/); Fusarium species, for example, such as large knives; Phytophthora species, for example, such as the genus Pythium, such as, for example, Pythium ultimum; Rhizoctonia , for example, the nucleus Small genus species, for example, rot and blight caused by seeds and soil caused by Sclerotium ro//Wz, and seedling diseases; for example, from the genus Rhododendron, for example , for example, cancer, insect skin and cluster leaf disease caused by Nectriagiz///gewfl; by, for example, Verticillium sp., for example, Verticillium dahliae (A/omYzWa) /βχα) caused by blight; by, for example, the outer genus of the genus, such as, for example, the abnormal outer sac

S 201200017 (Tb/7/zrma<^/br_^) caused by deformation of leaves, flowers and fruits; for example, Esca species, such as P/zaeomom-e/Za clamydospora and Phaeoacremonium aleophilum a disease of woody plants caused by medzYerr(10)(10); for example, a species of Botrytis, for example, a flower and a seed caused by Botrytis cinerea; for example, a species of Rhizoctonia, for example, Rhizoctonia solani; for example, the genus of the genus Helminthosporium (Jhelminthosporium solani), the disease of the plant qi1, from bacterial pathogens such as Xanthomonas For example, such as Xanthomonas campestris rice variety campe you & pv. or less zae); Pseudomonas species, for example, Pseudomonas syringae (Pseudomonas syringaepv) Iachrymcms) ·, the genus of the genus genus 'for example', such as the disease of Erwinia sinensis (five rwhia amy / ovona) bow | Priority is given to controlling the following soybean diseases: true functional diseases of leaves, stems, pods and seeds caused by, for example, the following pathogens: leaf-bearing leaf spot disease (•s/> ec. /iwzk/ma), anthracnose

Colletotrichum gloeosporoides dematium var. truncatum) ' Brown spot disease [iSepiork gfyckes], Cercospora leaf spot and Fusarium [C. cerevisiae A/A: wc/h7)], Fusarium oxysporum [漏^-^{Choanephora infundibulifera trispora (Syn.)) ' ^fL 43 201200017 Dactuliophora leaf spot disease [Sclerotium fulvum, downy mildew [Northeast genus Mflm/zwWca)] Drechslera wilt disease [Spirulina sinensis (Z) rec/w/era g (yc/m·)], worm eye leaf spot disease [Soybean cerevisiae • JO force > 2fl)], Small Phytophthora leaf spot disease [Shamrock glabrata (Ze/^W/zflerw/z·(10)irzyb/z·/)], leaf spot leaf spot disease [Soybean leaf spot mold (household / / 〇 right / <:^3 sci/aeco/a)], pod and stem wilt [Phomopsis sojae], transfusion disease {also, silk, scorpion Microsphaera, echinococcosis leaf spot [soybean] Helicobacter pylori (Pyre/ioc/meia (ycz'we·?)], Rhizoctonia oxysporum, cluster leaves, and spider silk wilt (Rhizobium ssp.), rust (Potas glabrata, mountain Horse rust fungus), spot disease [Dazhi disease round g/yczTze*?]], Fusarium oxysporum leaf blight [匍Mildew (Stemphylium 60 ^ 705wm)], scab [Cassia green Corynespora {Corynespora casslicola)]. Fungal diseases of roots and stem bases caused by, for example, the following pathogens: votes, root rot (1 Calonectria crotalariae), and good rot [C. edulis (Macr<9;?/zomz> 7a) Fusarium wilt, root rot, and bean bud and base rot [Frsarz'wm ori/zocerfls, semi-naked Fusarium (i^sYjfrzwm sewzYeciwm), Fusarium oxysporum) Fusarium equiseti)], Coccidial rot [Chosporium spore-forming rreWr]], New Phytophthora [invasion of new red shell vasz>2/ec^z)], bean smile and stem blight [String bean] Diaporthe phaseolorum], 1 ulcer disease (Diaporthe phaseolorum var. caulivora) ' Phytophthora rot [Agrobacterium tumefaciens 44

S 201200017 (Phyt〇Phth_ megasperman, brown stalk rot (Pg/Caf _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ (6)_ z>regw/_), Pythium debaryanum, 1 Pythium still _ surface m-Pythium oleifera], Rhizoctonia root rot, stem rot, and sputum disease Bacteria), Sclerotinia sclerotiorum (S. sclerotinia), Sclerotinia scab (5W (10) ro/plus of Sclerotinia), Rhizopus sp. root rot (root beaded emblem). The microorganism whose material is degraded or altered is a fungus. The active compound according to the present invention is preferably active against fungi, particularly molds, fungi which fading wood and destroying wood (Basidiomycetes). Examples which may be mentioned are the following genera Other microorganisms: Alternaria, such as Alternaria alternata plus r (10) r / (3 plus _); Fusarium, such as Aspengi (uspergiUus niger); Capsule, such as the ball shell (Chaet〇mium g /M(10)); Pseudomonas genus 'such as Helminthosporium (c〇m• Indo rib% like); Lentinus genus 'such as tiger skin mushroom gamma (10) ton coffee (four); Qinghui genus 'such as ash Green green emblem (Pem'cz'/Zz'w/wg/awcww); Polyporus, such as Pofyporws vers/co/or; Aphis genus, for example, wearing a short stalk emblem; Pythium genus, such as Sc/ero/^oma p ορ/π'/α; Trichoderma, such as the green wood emblem [Trichoderma viride). Furthermore, the active compounds according to the invention also have very good antimycotic activity. They have a broad range of antifungal activity, especially against dermatophytes and yeast, mold and biphasic fungi [eg against Candida species such as Candida albicans, Candida glabrata 2011200017 (C-glabrataj) Floccosum) > mmnmH^MM^mmUAspergillus / (10) coffee to), hairy fungus such as hairy fungus (JWc /, microsporum species such as M. cerevisiae (M.cr still push Microsporum cephalosporium (minus (10) p〇_(iv)(10)(iv). The enumerated fungi are for illustrative purposes only. The use of it's money limits the range of molds covered. When the active compound is used as a killing agent, The application rate can be varied within a relatively wide range. The rate of application of the active compound according to the invention is • when processing part of a plant such as a leaf: (U to 1 g/ha, compared Good for 1〇 to 1000g/ha, especially for 5〇; 〇〇g/ha (applied by water or drip, especially when using inerts such as asbestos or perlite) Rate of application); • When handling seeds: every 1 (nine) kilograms The amount is from 2 to 200 g, preferably from 3 to 150 g per 100 kg of seed, particularly preferably from 2.5 to 12.5 g per 1 kg of seed; • When treating the soil: 〇.1 to 1 〇, 〇〇〇克/ The hectares, preferably from i to 5000 g/ha. The rates of application are for illustration only and are not intended to limit the invention. The active compound or composition according to the invention may therefore be treated for a specific period after attack against the pathogen g. _ to protect plants. After treating plants with active compounds, the period of protection can usually be extended to Μ days, preferably days; especially good for u1〇 days, very good for 】

S 201200017 to 7 days; or after processing seeds, extend up to 2 days. Furthermore, by the treatment according to the present invention, the mycotoxin content in the harvested material and the foodstuff and feed prepared therefrom can be reduced. In particular, the following may be mentioned as the following mycotoxins: deoxixenivalenol (DON), decidone, 15-Ac-DON, 3-Ac -DON, T2- and HT2-toxin, fumonisine, zearaienon, moniliformin, fusarin, diethyl hydrazine Toxin (diaceotoxyscirpenol) (DAS), beauvericin, enniatin, fusar〇pr〇iiferin, fusarenol, ochratoxins , baromycin, ergot alkaloids and xanthotoxin; these mycotoxins are produced by the following fungi: Fusarium species such as Fusarium oxysporum

Addition), Fusarium oxysporum (F, Fusarium oxysporum (F-like e), Fusarium oxysporum (F cw / Institute, Gramineae graminearum (γ grflfmz·rwm) (Matrogana), wood thief Spores (F is called deduction), only fujikoroi, F. musarum, F. oxysporum, Fpw/i/eraiww, Fusarium oxysporum (π from) , only pewi/ogramz·rww, Fusarium oxysporum (7), such as ~ (10), Fusarium oxysporum (β sc / rp /), Fusarium sphaeroides (F, rot

Bacillus (β still / (10) /), M. sphaeroides (EF, Fusarium oxysporum (F), Trichoderma genus, Fusarium oxysporum (F veriz.c / W/o/i^), etc.; and genus genus, Penicillium, C. avcepvwrpwrea, Stachybotrys, etc. 201200017 The above plants can be used according to the formula (i) The maleimide quinones are particularly advantageously treated according to the invention. The above-mentioned preferred range of active persons or compositions are also suitable for the treatment of their plants. Special emphasis should be placed on: Composition treatment plant: :, [Embodiment] Preparation example 1

Ch3 An amount of 10 g (52.9 mmol) of N-mercapto-dihydromaleimide was introduced into 1 ml of anhydrous methanol. This suspension was blended dropwise with 8 455 g (111.1 mmol) of thiourea in 1 mL of an anhydrous decyl alcohol solution at 2 to 3.0. After about 20 minutes, a yellow crystal sink was formed from the solution at 〇_5〇c. After further stirring at this temperature for 1 minute, the crystals were separated by suction filtration, and the mother liquor was further blended with 200 liters of cold diethyl ether, followed by separation of the crystal precipitate by suction. After drying, 13 5 g (74 3% of theory) of two gasified [〇_methyl-2,5-diketo-2,5-dihydro-1Η-pyrrole_3,4-diyl) disulfide was obtained. Alkyldiyl] bis(amine oxime), dazzle 163164. Hey. Example 27

S 201200017

Amount of 0.20 g (〇_6 mmol) of dichlorinated [(1_methyl-2,5-dione-2,5-dihydro-1H-pyrrole-3,4-diyl) Disulfanediyl] bis(amine oxime) was mixed with 0.12 g (1.2 mmol) of KHC03, and this mixture was introduced under stirring with 2 ml of H2 〇 / 4 ml of ice. Stirring until ice is dissolved, the red brick color crystals are separated by filtration by suction filtration, and washed with ice water; after drying, 50 mg (38.2% of theory) 4-·[[amino(imino)indenyl]thio group is obtained. }-1_Methyl-2,5-diketo-2,5-dihydro·ιη-pyrrole-3-thiolate, m.p. 150-152oC. Example 72

Introduce the amount of 〇2〇g (〇.6 mmol) in 4 ml of water.

49 201200017 The second silver (1+) 1-methyl-2,5-dione-2,5-dihydro-111-pyrrole-3,4-bis (thiolate). Example 89

Ch3 to make 1.33 g (4 mmol) of dichloro[(1-indolyl-2,5-diketo-2,5-dihydro-1H-pyrrole-3,4-diyl) The sulfanediyl] bis(amino sulfiminium) was dissolved in water, excess aqueous ammonia was added, and the system was filtered. The filtrate was acidified with 5 ml of concentrated hydrochloric acid. The fresh green precipitate was separated by filtration through suction filtration, washed with water and a small amount of decyl alcohol. After drying, 0.51 g (72.8% of theory) of 1-mercapto-3,4-dithio-1H-pyrrole-2,5- Diketone, melting point 145-148 ° C. Similarly to the above examples, and in accordance with the general description of the process according to the invention, the compounds of formula (I) shown in Table 1 below can be prepared. Table 1

K (2/n X)m (!) R1 For the sake of brevity, the subgroup to which the compound belongs, i.e., the compound of formula (la), (lb) or (Ic), is indicated in each case.

S 50 201200017 R\ R4 .N-R2 yK 〇R\ R4 N-R2 .〇R ' ,9 s I N-R1 (2/n X)mrs^j ( 1 I N-R1 (2/n X) m R6 T N-R1 , N-<\ 〇R?/ , N-R9 i〇0 R8 (la) (lb) (Ic) Instance type (2/n X)m R1 R2 R3 R4 R5 R6 R7 R8 R9 Melting point (°C) 1 (la) 2C1~ Me Η Η Η Η Η Η Η 163 163-164 2 (la) 2C1" (lS)-l-(4-Phenylphenyl)acetamidine - Η Η Η Η Η Η Η Η 188-192 3 (la) 2C1" 1 -(4-Phenylphenyl)ethyl Η Η Η Η Η Η Η 168 168-195 4 (la) 2C1~ 1-Phenylethyl Η Η Η Η Η Η Η 177 177-181 5 (la) 2C1" 4-amine sulfonyl phenyl hydrazine Η Η Η Η Η Η >250 6 (la) 2d- 2-oxoethyl Η Η Η Η Η 167 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 172 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 167 -2 phenyl Η Η Η Η Η Η Η 224 224-250 10 (la) 2d- 3,4-di-phenylphenyl Η Η Η Η Η Η Η 193 193-195 11 (la) 2C plant 2,4 - 2 1 Η Η Η Η Η Η Η Η >250 12 (la) 2C plant (phenylsulfonyl) amide Η Η Η Η Η Η Η 155-158 13 (la) 2C1&q Ot 190 190 190 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 198 (la) 2d- butyl Η 161 161 161 161 161 161 161 161 161 161 161 161 161 161 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 171 152 152-164 18 (la) 2d- 2-methylpropyl Η Η Η Η Η Η Η 143 143-172 19 (la) 2d- 2,2-di-mercaptopropyl Η Η Η Η Η Η Η 172 172-174 20 (la) 2CF iPr 162 Η 162 162 Η Η Η 162 162-165 21 (la) 2d-cyclopropyl Η Η Η Η Η Η Η 159 159-164 22 (la) 2C1_ cyclopropyl hydrazine 2 1 Η Η Η Η Η 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 La) 2C1" Me Η Η Me Me Η Η Me Me 135-160 26 (lb) Me Et Η Et Η 124-260 27 (lb) Me Η Η Η Η 150-152 28 (lb) Me Η Η Me Η 137 -139 29 (lb) 2-methoxyethyl Η Η Η Η 139-144 30 (lb) Me Η Η Et Η 125-133 31 (lb) 3-(trifluoromethyl)cyclohexyl Η Η Η 129 -131 51 20120001 7 Example type (2/n X)m R1 R2 R3 R4 R5 R6 R7 R8 R9 Melting point (0C) 32 (lb) 3,4-digas base HHHH >275 33 db) Me HH Ph H 95-102 34 (lb) Et HHHH 152-154 35 db) Me Prl H Pr H Oil 36 (lb) Me HH Bz H 130-138 37 (lb) HHHHH >210 38 db) Cyclopropyl fluorenyl HHHH 138-139 39 db Pr HHHH 153-158 40 (lb) Cyclopropyl HHHH 163-168 41 (lb) Bz HHHH 142-149 42 db) iPr HHHH 155-158 43 db) Cyclohexyl HHHH 142-143 44 db) 3,5- Diphenylphenyl HHHH 182-220 45 db) 2,4-digas base HHHH 175-193 46 db) 2-methylpropyl HHHH 141-149 47 db) Trifluoromethyl)phenyl HHHH 170-174 48 (lb) Me HH Me Me 141-143 49 db) Butyl HHHH 149-150 50 db) 1-(4-Phenylphenyl)ethyl HHHH 155-159 51 (lb) (1S)-1 -(4 -gashyl)ethylHHHH 161-172 52 db) 1-phenylethyl HHHH 154-157 51 (lb) (1S)-1 -(4-phenylphenyl)ethyl HHHH 152-156 54 (10) 4- Amine sulfonylphenyl HHHH >290 55 db) (phenylsulfonyl)amino HHHH 189-193 57 (la) 2d- Me HH Me HHH Me H 175-193 58 da) 2CT Me HH iPr HHH iPr H 141-148 59 da) 2d- Me HH Ph HHH Ph H 113-118 60 da) 2d- Me HH tBu HHH tBu H 121-123 61 (la) 2C1~ Me HH Et HHH Et H 136-141 62 (la) 2d- Me HH Bz HHH Bz H 162-166 63 da) 2d- Me Me H iPr H Me H iPr H 123-125 64 da) 2d' Me HH Pr HHH Pr H 154-156 65 da) 2C1" Me Et H Et H Et H Et H 126-128 66 da) 2C1_ Me Pr H Pr H Pr H Pr H 103-105 67 db) Me HH iPr H 69-72 68 db) Me HH Pr H 145-260 69 db) Me HH tBu H 134-260 70 Db) Me Me H iPr H 146-260 71 db) 2,2-dimethylmethylpropyl HHHH 161-164 72 (10) 2AgT Me oil 73 (la) 2ΒΓ Me HHHHHHHH 116-150 s 52 201200017 Example type (2/ n X)m R1 R2 R3 R4 R5 R6 R7 R8 R9 Melting point (0C) 74 (Ic) Ζη2τ Me >244 75 (Ic) 2Α?Γ Et oil 76 da) 2ΒΓ Me HH Me HHH Me H 148-154 77 ( La) 2ΒΓ Me HH Me Me HH Me Me 179-185 78 (la) 2Β H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H 109 82 (la) 2ΒΓ Me HH Bz HHH Bz H 152-159 83 (la) 2ΒΓ Me HH tBu HHH tBu H 121-124 84 (la) 2ΒΓ Me Et H Ht H Et H Et H 158-160 85 (10) 2ΒΓ Me Pr H Pr H Pr H Pr H 118-120 86 da) 2ΒΓ Me Me H iPr H Me H iPr H 156-161 87 (lb) Me Me H Me H 119-130 88 (la) 2ΒΓ Me Me H Me H Me H Me H 153-158 89 (Ic) 2ΕΓ Me 145-148

Me = methyl, Et = ethyl, Pr = n-propyl, iPr = prop-2-yl, tBu = tert-butyl, ph = phenyl, Bz = benzyl Example of use Example A: Phytophthora test (tomato / protective solvent: 24.5 parts by weight of propylene with 24.5 parts by weight of decyl ether amine emulsifier: 1 part by weight of aryl aryl polyethylene glycol ether to make 1 part by weight of active compound and the amount of solvent and emulsifier Mix and dilute the concentrate to the desired concentration with water to make a suitable formulation of the active compound. To test the protective activity, the young plant is sprayed with the active compound preparation at the rate of application. After the spray coating is dried, the aqueous solution of the Phytophthora infestans suspension is inoculated into the plant. "The degree will be about 20. Please keep the relative humidity until 接. After 3 days of inoculation, go to the area. 〇% means efficacy equivalent 53 201200017 in the control group, and 100% efficacy means no infestation observed. In this test, at the concentration of 250 ppm active compound, compounds 1, 6, 8, 10, 17, according to the invention 18, 22, 23, 26, 27, 28, 32 and 37 exhibited efficacy of 70% or more. Example B: Black spot test (apple) / protective solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethyl Acetamide emulsifier: 1 part by weight of alkyl aryl polyethylene glycol lightly mixing 1 part by weight of the active compound with the solvent and emulsifier, diluting the concentrate with water to the desired concentration to produce the active compound When the protective activity is to be tested, the young plant is sprayed with the active compound preparation at the application rate. After the spray coating is dried, the apple spot disease pathogen, Mycobacterium sphaeroides (Fewiwrk/sporospore suspension aqueous solution) is inoculated. On the plant, then put the plant It was placed in an incubator at about 20 ° C and a relative humidity of about 90% for 1 day. After 10 days of inoculation, the evaluation was carried out; here, 0% means that the potency is equivalent to the control group, and 100% of the effect means that no observation is observed. Intrusion. In this test, compounds 1, 6, 8, 10, 17, 22, 26, 27, 28, 29, 30, 3, 32, 33, 34, 35 according to the invention at a concentration of 250 ppm active compound , 36, 37, 38, 39, 40, 41, 42 and 44 show 70% or more of the effectiveness.

S 54

Claims (1)

201200017 VII. Scope of application: 1. The use of a maleidin salt of the following formula (I) for controlling phytopathogenic fungi, In the formula, (a) Y1 is a group R5, /R4 s having the following formula (II). NR R γ2 is a group having the following formula (m): rVr8 R6 (III) > m is 1, n is X Ionic charge, and X is an anion selected from CT or ruthenium, or (b) Y1 is a group R5\ /R4 S of the following formula (II), NIR in I ϊ is ο mY and 55 201200017 or (c) Yl is -s~, Y2 is, and X 1,11 is the ionic charge of X, and is a cation selected from the group consisting of H+, Ag+, c〇2+ Νί^ ' /-7 2+ M, Zn, Cu2H Fe2+, Mn2+, R1 is 虱, or is replaced by the same or different halogen, _ substituent, or as many times as possible (10) alkyl; ^ΐ ring _CVC2· silk, each of which is required to be the same or = Substituents such as crc4-alkyl or CrCV haloalkyl are substituted—human, or aryl, aryl-(CrC4-alkyl) or arylsulfonylamino, each of which is optionally the same or different in the aryl moiety. Substituting a substituent such as Ci_c4_alkyl Ci-C4__alkyl, -COR11 or a Si-amino group - or multiple times, R2, R3, R4, R5, R6, R7, R8 and r9 are independently hydrogen, C1 -C6-alkyl, or phenyl or benzyl, each being the same or as needed Substituted one or more substituents such as dentate, CVCV alkyl, CVCr alkoxy or CrCV thiol, for hydrogen, crCV alkyl, CrC4_alkylcarbonyl, or optionally by _, Ci C4 or GC; a substituent such as 4-dentate is substituted with one or more aryl groups, / is an L group, a C1-C4-alkyl group or a Ci-C4-carbon group. S 56 201200017 2. The use according to item 1 of the scope of the patent application, characterized in that R1 is hydrogen; or is replaced by the same or different substituents such as fluorine, chlorine, bromine, ... (7) and/or -COR11, as needed. a plurality of Cl_C6_alkyl groups; or a CVC7-cycloalkyl group or a C3_C7-cycloalkyl-CrC2-alkyl group, each of which may be substituted by a substituent such as the same or different chlorine, methyl or trifluoromethyl group, or Multiple times; or phenyl, phenyl-(CrC4_alkyl) or strepylsulfonylamino, each being the same or different, fluorine, gas, bromine, sulfhydryl, trifluoromethyl, -COR11 and / or a substituent such as a sulfonamide group is substituted one or more times, and R 2 , R 3 , R 4 , R 5 , R 6 , R 8 and R 9 are each independently hydrogen, C 1 -C 4 -deryl, phenyl or a benzyl group, and R 1 G is Hydrogen, mercapto, ethyl, hydrazine carbonyl or ethyl carbonyl, or may be substituted one or more times with a substituent such as fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl or trifluoromethyl, if necessary Phenyl, R11 is hydroxy, decyl, ethyl, methoxy or ethoxy; if X is an anion, then X is gas; right X is 11⁄4 ion' then X is H+, Ag+, Fe2+, Mn2+ or Zn2+. 3. Use according to item 1 or 2 of the scope of the patent application, characterized in that R1 is hydrogen; or, if desired, the same or different fluorine, chlorine, hydroxyl, decyloxy, ethoxy, mercaptocarbonyloxy and/ Or a substituent such as a carboxyl group substituted with one or more CrCV alkyl groups; or a cyclopropyl fluorenyl group or CrC substituted one or more times with a substituent such as the same or different gas, mercapto or difluoroindenyl group; A cycloalkyl group, either a phenyl group, a benzyl group, an anthracene-ethyl group, a stilbene ethyl group or a 2-mercapto-2-ethyl group, each of which may be the same or different, 201200017 gas, desert, A Substituting, trifluoromethyl, -COR substituents one to three times, R2, R3, R4, R5, r6, and/or sulfonylamino groups, etc., _, second or third - R, R and R9 Independently hydrogen, methyl, ethyl, n-propyl, isopropyl, n- or butyl, R is hydrogen, methyl or methylcarbonyl, or phenyl, R11 is hydroxy or T-oxy; if X is For anion, X is gas; if X is a cation' then X is Ag+, Mn2·^ Zn2+. 4. A composition for controlling a phytopathogenic fungus, characterized in that at least one of them is in accordance with the scope of the patent application! The maleic amine salt of the formula (1) is added with a extender and/or an interface active material. 5. A method for controlling phytopathogenic true g, which is characterized in that the maleramamine salt of the formula (1) according to claim 1 of the patent application is delivered to the fungus and/or its habitat. 6. - a maleic imide salt of the following formula (IV), (2/n X^)m (IV) where S 58 201200017 R is 虱m or is substituted one or more times by the same or different halogen, -or丨0a and/or f〇R, etc., as desired. C1_C8_alkyl; C3-C7-decyl or crcv cycloalkyl-CrC2_alkyl, each of which may be substituted one or more times by substituents such as the same, Cl<v alkyl or Ci_C4_haloalkyl, as desired Or an aryl, aryl-(CrCr alkyl) or arylsulfonylamino group, each optionally having the same or different halogen, CrC4-alkyl, CrCV-alkyl, _c〇Rna or sulfonate in the aryl moiety Substituted with a substituent such as amidino group for one or more times), f, R5a, R6a, R7a, ... and R9a are each independently hydrogen, alkyl, or phenyl or benzyl, each being the same or different as desired. a substituent such as a Ci-cv alkyl group, a (:^^ alkoxy group or a Ci_Q_alkylthio group) substituted one or more times, wherein J R1 is hydrogen, methyl, hydroxymethyl or methylcarbonyloxymethyl , gas toluene or methoxymethyl and xa are gas, then R2a, R3a, ι〇R is not hydrogen at the same time, 匸4 alkyl or crC4-i| alkyl and other substituents are substituted for one or more aromatic C . Base C1-C4-垸 base, Cl_c4_ burn-in, or as needed And R is a radical, a C1-C4-alkyl group or a CrC4-alkoxy group, m is an ionic charge of 1' η as Xa, and X is an anion selected from Cr or ruthenium. Maleic imide salts, 59 201200017 Ο (V) wherein lb ' R is hydrogen; or a crc8-alkyl group optionally substituted one or more times with the same or different halogen, -R10b and/or -C0Rllb; c3-cv cycloalkyl or CrCV cycloalkyl-Crc2_alkyl, each of which is replaced by a substituent such as the same or different dentin, CrC4.alkyl or crC4-haloalkyl, etc., in addition to the aryl group, aryl-(C1-C4) - an alkyl group or a aryl group - the aryl moiety is optionally substituted with a substituent such as the same or different halogen, Ci-CV alkyl, CrC4-dentyl, _c〇Riib or sulfonylamino group. One or more times, R, ^, R4b and R5b are independently of each other hydrogen, crc6-sayyl, or phenyl 3 ^, each being the same or different halogen, crc4-alkyl, i irC4i"b alkoxy Or a substituent such as a CrCr alkylthio group is substituted one or more times, and if R+ is hydrogen, a fluorenyl group, a hydroxymethyl group, a fluorenylcarbonyloxymethyl group, a chloromethyl group, a benzyl group, a stupid group or a methoxy group Base, then R2b, R3b, 尺 盥 are not hydrogen at the same time, 〃 R1 〇 b > 3 p _ ', 4 · alkyl, CrCV alkyl carbonyl, or as needed _ prime, ^ 4, elemental or CrC4 · Substituting one or more substituents such as a dentate group The second aromatic R is a thiol group, a crc4_homobase or a Ci_C4_ alkoxy group. 201200017 8. —The maleic imide salt of the following formula (VI), 0 (2/n Xc)m (VI) wherein Rle is hydrogen; or a CrC8-alkyl group substituted one or more times by a substituent such as the same or different halogen, _OR】〇c and/or _C0Rlle, as appropriate; C3 -C7-cycloalkyl or C3_C7-cycloalkyl-crc2-alkyl, each being substituted by the same or different substituents such as iS, CrC4-alkyl or CrC4-alkyl, or eve-human' or square The aryl group, the aryl group (CrCr alkyl group) or the aryl sulfoxide group can be replaced by the same or different halogen, Ci_C4_alkyl, CrC4__alkyl, _C〇RUa or sulfonylamino group, etc., in the aryl moiety. Substituting one or more times, R1〇c is hydrogen, CVCV alkyl, CrCr alkylcarbonyl, or optionally substituted by halogen, q-cv alkyl or Cr (Vil alkyl, etc., one or more substituents) 'R1 is a hydroxyl group, a CVCV alkyl group or a Ci_C4_alkoxy group, m is 1, n is an ionic charge of y, and Xc is from Ag+, C〇2+, Cu2+, #, Mn2+, Ni2+, 2+ and The cation of T, wherein if & is hydrogen, fluorenyl, hydroxydecyl, fluorenyl methoxy fluorenyl, fluoromethyl, benzyl, phenyl or anthracenyl, then X. Not Ag+. 201200017 IV Designated representative map: (1) Designation of the case The representative picture is: No. (2) The symbol of the symbol of this representative figure is simple: Benefit 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: None S